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AR035819A1 - 2- (REPLACED AMINO) -BENZOXAZOL SULFONAMIDES, HIV PROTEASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS THAT INCLUDE SUCH COMPOUNDS, IN VITRO METHOD TO INHIBIT THE RETROVIRAL REPLICATION AND USE OF SUCH COMPOUNDS IN THE LABOR COMPOSITIONS - Google Patents

2- (REPLACED AMINO) -BENZOXAZOL SULFONAMIDES, HIV PROTEASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS THAT INCLUDE SUCH COMPOUNDS, IN VITRO METHOD TO INHIBIT THE RETROVIRAL REPLICATION AND USE OF SUCH COMPOUNDS IN THE LABOR COMPOSITIONS

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Publication number
AR035819A1
AR035819A1 ARP020101301A ARP020101301A AR035819A1 AR 035819 A1 AR035819 A1 AR 035819A1 AR P020101301 A ARP020101301 A AR P020101301A AR P020101301 A ARP020101301 A AR P020101301A AR 035819 A1 AR035819 A1 AR 035819A1
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AR
Argentina
Prior art keywords
4alkyl
het2
alkyl
het1
aryl
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ARP020101301A
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Spanish (es)
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Tibotec Pharm Ltd
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Publication date
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Publication of AR035819A1 publication Critical patent/AR035819A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Virology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

2-(Amino sustituido)-benzoxazol sulfonamidas, inhibidoras de amplio espectro de la proteasa del HIV, que tienen la fórmula (1), sus N-óxidos, sales, formas estereoisoméricas, mezclas racémicas, prodrogas, ésteres, metabolitos, en donde: R1 y R8 son cada uno de ellos e independientemente entre sí, hidrógeno, alquilo de C1-6, alquenilo de C2-6, aril C1-6alquilo, C3-7cicloalquilo, C3-7cicloalquilC1-6alquilo, arilo, Het1, Het1C1-6alquilo, Het2, Het2C1-6alquilo; R1 también puede ser un radical de la fórmula (2) en la cual: R9, R10a y R10b, son cada uno de ellos e independientemente entre sí, hidrógeno, C1-4alquiloxicarbonilo, carboxilo, aminocarbonilo, mono- o di(C1-4alquil)carbonilo, C3-7cicloalquilo, C2-6alquenilo, C2-6alquinilo o alquilo de C1-4 opcionalmente sustituido con arilo, Het1, Het2, C3-7 cicloalquilo, C1-4 alquiloxicarbonilo, carboxilo, aminocarbonilo, mono- o di(C1-4alquil)aminocarbonilo, aminosulfonilo, C1-4alquilS(O)t, hidroxi, ciano, halógeno o amino opcionalmente mono- o di sustituido, estando los sustituyentes, cada uno de ellos e independientemente entre sí, seleccionados de entre el grupo consistente en alquilo de C1-4, arilo, arilC1-4alquilo, C3-7cicloalquilo, C3-7cicloalquilC1-4alquilo, Het1, Het2, Het1C1-4alquilo y Het2C1-4alquilo; con lo cual R9 y R10a y los átomos de carbono a los cuales están fijados pueden también formar un radical C3-7cicloalquilo; cuando L es -O-C1-6 alcanodiil-C(=O)- o -NR8-C1-6alcanodiil-C-(=O)-, entonces R9 también puede ser oxo; R11a es hidrógeno, C2-6alquenilo, C2-6alquinilo, C3-7cicloalquilo, arilo, aminocarbonilo opcionalmente mono o di sustituido, aminoC1-4carboniloxi opcionalmente mono- o di-sustituido, C1-4alquiloxicarbonilo, ariloxicarbonilo, Het1 oxicarbonilo, Het2 oxicarbonilo, ariloxicarbonilC1-4alquilo, arilC1-4 alquiloxicarbonilo, C1-4alquilcarbonilo, C3-7cicloalquilcarbonilo, C3-7 cicloalquilC1-4alquiloxicarbonilo, C3-7cicloalquilcarboniloxi, carboxiC1-4 alquilcarboniloxi, C1-4alquilcarboniloxi, arilC1-4alquilcarboniloxi, ariloxicarboniloxi, Het1 carbonilo, Het1 carboniloxi, Het1 C1-4alquiloxicarbonilo, Het2 carboniloxi, Het2-C1-4alquilcarboniloxi, Het2C1-4alquiloxicarboniloxi, o C1-4 alquilo opcionalmente sustituido con arilo, ariloxi, Het2, halógeno hidroxi, estando los sustituyentes en los grupos amino, cada uno de ellos e independientemente entre sí seleccionados de entre el grupo consistente en alquilo de C1-4, arilo, arilC1-4alquilo, C3-7cicloalquilo, C3-7cicloalquilC1-4alquilo, Het1, Het2, Het1C1-4 alquilo y Het2C1-4 alquilo; R11b es hidrógeno, C3-7cicloalquilo, C2-6alquenilo, C2-6alquinilo, arilo, Het1, Het2 o alquilo de C1-4 opcionalmente sustituido con halógeno, hidroxi, C1-4alquilS(=O)t, arilo, C3-7cicloalquilo, Het1, Het2, amino opcionalmente mono- o di sustituido estando los sustituyentes, cada uno de ellos e independientemente entre si seleccionados de entre el grupo consistente en alquilo de C1-4, arilo, arilC1-4alquilo, C3-7cicloalquilo, C3-7 cicloalquilC1-4alquilo, Het1, Het2, Het1C1-4alquilo y Het2C1-4alquilo; pudiendo R11b estar ligado al resto de la molécula por intermedio de un grupo sulfonilo; cada uno de los t, independientemente entre sí, vale 0, 1 o 2; R2 es hidrógeno o alquil de C1-6; L es -C(=O)-, -O-(=O)-, -NR8-C(=O)-, -O-C1-6alcanodiil-C(=O)-, -NR8-C1-6alcanodiil-C(=O)-, -S(=O)2-, -O-S(=O)2, NR8-S(=O)2, en lo cual sea el grupo C(=O) sea el grupo S(=O)2 está fijado a la parte NR2; con lo cual la parte alcanodiilo está opcionalmente sustituido con arilo, Het1, Het2; R3 es alquilo de C1-6, arilo, C3-7cicloalquilo, C3-7cicloalquilC1-4alquilo, o arilC1-4alquilo; R4 es hidrógeno, C1-4alquiloxicarbonilo, carboxilo, aminocarbonilo, mono- o di(C1-4alquil)aminocarbonilo, C3-7cicloalquilo, C2-6 alquenilo, C2-6 alquinilo, o C1-6 alquilo opcionalmente sustituido con uno o más sustituyentes, cada uno de ellos e independientemente entre sí seleccionados de entre el grupo consistente en arilo, Het1, Het2, C3-7cicloalquilo, C1-4alquiloxicarbonilo, carboxilo, aminocarbonilo, mono- o di(C1-4alquil)aminocarbonilo, aminosulfonilo, C1-4 alquilS(=O)t, hidroxi, ciano, halógeno y amino opcionalmente mono o disustituido, estando los sustituyentes, cada uno de ellos e independientemente entre sí seleccionados de entre el grupo consistente en alquilo C1-4, arilo, arilC1-4alquilo, C3-7cicloalquilo, C3-7cicloalquilC1-4alquilo, Het1, Het2, Het1C1-4alquilo y Het2C1-4 alquilo; A es C1-6 alcanodiilo, -C(=O)-, -C(=S)-, -S(=O)2, C1-6alcanodiil-C(=O)-, C1-6alcanodiil-C(=S)- o C1-6alcanodiil-S(=O)2-; estando el punto de fijación al átomo de nitrógeno es el grupo C1-6alcanodiilo en aquellas partes que contienen dicho grupo; R5 es hidrógeno, hidroxi, alquilo de 1 a 6 átomos de carbono; Het1C1-6alquilo, Het2C1-6alquilo, aminoC1-6alquilo, pudiendo el grupo amino estar mono o disustituido con alquilo de C1-4; R6 es C1-6alquiloxi, Het1, Het1 oxi, Het2, Het2 oxi, arilo, ariloxi; y en el caso en que -A- no es C1-6alcanodiilo, entonces R6 también puede ser C1-6alquilo, Het1-C1-4 alquilo, Het1 oxiC1-4alquilo, Het2C1-4alquilo, Het2 oxiC1-4alquilo, arilC1-4alquilo, ariloxiC1-4alquilo o aminoC1-4alquilo; pudiendo cada uno de los grupos amino en la definición de R6, estar opcionalmente sustituido con uno o más sustituyentes, cada uno de ellos independientemente entre sí seleccionados de entre el grupo consistente en alquilo de C1-4, C1-4 alquilcarbonilo, C1-4alquiloxicarbonilo, arilo, arilcarbonilo, ariloxicarbonilo, Het1, Het2, arilC1-4alquilo, Het1C1-4alquilo o Het2C1-4alquilo; y -A-R6 también puede ser hidroxiC1-4alquilo; R5 y-A-R6 tomados conjuntamente con el átomo de nitrógeno al cual están unidos, pueden también formar Het1 o Het2. También se dan a conocer: composiciones farmacéuticas que comprenden dichos compuestos, un método in vitro para inhibir la replicación retroviral y el uso de dichos compuestos en la fabricación de medicamentos.2- (Substituted amino) -benzoxazole sulfonamides, broad-spectrum inhibitors of the HIV protease, which have the formula (1), their N-oxides, salts, stereoisomeric forms, racemic mixtures, prodrugs, esters, metabolites, wherein: R1 and R8 are each and independently of each other, hydrogen, C1-6 alkyl, C2-6 alkenyl, C1-6 aryl alkyl, C3-7cycloalkyl, C3-7cycloalkylC1-6alkyl, aryl, Het1, Het1C1-6alkyl, Het2, Het2C1-6alkyl; R1 can also be a radical of the formula (2) in which: R9, R10a and R10b are each and independently from each other, hydrogen, C1-4alkyloxycarbonyl, carboxyl, aminocarbonyl, mono- or di (C1-4alkyl) ) carbonyl, C3-7cycloalkyl, C2-6alkenyl, C2-6alkynyl or C1-4 alkyl optionally substituted with aryl, Het1, Het2, C3-7 cycloalkyl, C1-4 alkyloxycarbonyl, carboxyl, aminocarbonyl, mono- or di (C1- 4alkyl) aminocarbonyl, aminosulfonyl, C1-4alkyl (O) t, hydroxy, cyano, halogen or optionally mono- or di-substituted amino, the substituents, each being independently of each other, selected from the group consisting of alkyl of C1-4, aryl, arylC1-4alkyl, C3-7cycloalkyl, C3-7cycloalkylC1-4alkyl, Het1, Het2, Het1C1-4alkyl and Het2C1-4alkyl; whereby R9 and R10a and the carbon atoms to which they are attached can also form a C3-7cycloalkyl radical; when L is -O-C1-6 alkanediyl-C (= O) - or -NR8-C1-6 alkanediyl-C - (= O) -, then R9 can also be oxo; R11a is hydrogen, C2-6alkenyl, C2-6alkynyl, C3-7cycloalkyl, aryl, optionally mono- or di-substituted aminocarbonyl, optionally mono- or di-substituted aminoC1-4carbonyloxy, C1-4alkyloxycarbonyl, aryloxycarbonyl, Het1 oxycarbonyl, Het2-oxycarbonyl 4alquilo, arilC1-4 alkyloxycarbonyl, C1-4alquilcarbonilo, C 3-7 cycloalkylcarbonyl, C3-7 cicloalquilC1-4alquiloxicarbonilo, C3-7cicloalquilcarboniloxi, carboxiC1-4 alkylcarbonyloxy, C1-4alquilcarboniloxi, arilC1-4alquilcarboniloxi, aryloxycarbonyloxy, Het 1 carbonyl, Het 1 carbonyloxy, Het 1 C1- 4-alkyloxycarbonyl, Het2 carbonyloxy, Het2-C1-4alkylcarbonyloxy, Het2C1-4alkyloxycarbonyloxy, or C1-4 alkyl optionally substituted with aryl, aryloxy, Het2, hydroxy halogen, the substituents being in the amino groups, each of them and independently from each other selected from among the group consisting of C1-4 alkyl, aryl, arylC1-4alkyl, C3-7cycloalkyl, C3-7cycloalkylC1-4alkyl, Het1, Het 2, Het1C1-4 alkyl and Het2C1-4 alkyl; R11b is hydrogen, C3-7cycloalkyl, C2-6alkenyl, C2-6alkynyl, aryl, Het1, Het2 or C1-4 alkyl optionally substituted with halogen, hydroxy, C1-4alkyl (= O) t, aryl, C3-7cycloalkyl, Het1 , Het2, optionally mono- or di substituted amino being the substituents, each and independently selected from among the group consisting of C1-4 alkyl, aryl, arylC1-4alkyl, C3-7cycloalkyl, C3-7 cycloalkylC1- 4alkyl, Het1, Het2, Het1C1-4alkyl and Het2C1-4alkyl; R11b may be linked to the rest of the molecule through a sulfonyl group; each of the t, independently of each other, is worth 0, 1 or 2; R2 is hydrogen or C1-6 alkyl; L is -C (= O) -, -O - (= O) -, -NR8-C (= O) -, -O-C1-6alkanediyl-C (= O) -, -NR8-C1-6alkanediyl- C (= O) -, -S (= O) 2-, -OS (= O) 2, NR8-S (= O) 2, in which group C (= O) is group S (= O) 2 is fixed to part NR2; whereby the alkanediyl part is optionally substituted with aryl, Het1, Het2; R3 is C1-6 alkyl, aryl, C3-7cycloalkyl, C3-7cycloalkylC1-4alkyl, or arylC1-4alkyl; R4 is hydrogen, C1-4alkyloxycarbonyl, carboxyl, aminocarbonyl, mono- or di (C1-4alkyl) aminocarbonyl, C3-7cycloalkyl, C2-6 alkenyl, C2-6 alkynyl, or C1-6 alkyl optionally substituted with one or more substituents, each and independently from each other selected from the group consisting of aryl, Het1, Het2, C3-7cycloalkyl, C1-4alkyloxycarbonyl, carboxyl, aminocarbonyl, mono- or di (C1-4alkyl) aminocarbonyl, aminosulfonyl, C1-4alkyl (= O) t, hydroxy, cyano, halogen and amino optionally mono or disubstituted, the substituents, each being independently selected from each other from the group consisting of C1-4 alkyl, aryl, arylC1-4alkyl, C3- 7cycloalkyl, C3-7cycloalkylC1-4alkyl, Het1, Het2, Het1C1-4alkyl and Het2C1-4alkyl; A is C1-6 alkanediyl, -C (= O) -, -C (= S) -, -S (= O) 2, C1-6alkanediyl-C (= O) -, C1-6alkanediyl-C (= S ) - or C1-6alkanediyl-S (= O) 2-; the point of attachment to the nitrogen atom being the C1-6alkanediyl group in those parts containing said group; R5 is hydrogen, hydroxy, alkyl of 1 to 6 carbon atoms; Het1C1-6alkyl, Het2C1-6alkyl, aminoC1-6alkyl, the amino group may be mono- or disubstituted with C1-4alkyl; R6 is C1-6alkyloxy, Het1, Het1 oxy, Het2, Het2 oxy, aryl, aryloxy; and in the case where -A- is not C1-6alkanediyl, then R6 can also be C1-6alkyl, Het1-C1-4 alkyl, Het1 oxiC1-4alkyl, Het2C1-4alkyl, Het2 oxiC1-4alkyl, arylC1-4alkyl, aryloxyC1 -4alkyl or aminoC1-4alkyl; each of the amino groups may be in the definition of R6, optionally substituted with one or more substituents, each independently selected from each other from the group consisting of C1-4 alkyl, C1-4 alkylcarbonyl, C1-4alkyloxycarbonyl , aryl, arylcarbonyl, aryloxycarbonyl, Het1, Het2, arylC1-4alkyl, Het1C1-4alkyl or Het2C1-4alkyl; and -A-R6 can also be hydroxyC 1-4 alkyl; R5 and -A-R6 taken together with the nitrogen atom to which they are attached, can also form Het1 or Het2. Also disclosed are: pharmaceutical compositions comprising said compounds, an in vitro method for inhibiting retroviral replication and the use of said compounds in the manufacture of medicaments.

ARP020101301A 2001-04-09 2002-04-09 2- (REPLACED AMINO) -BENZOXAZOL SULFONAMIDES, HIV PROTEASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS THAT INCLUDE SUCH COMPOUNDS, IN VITRO METHOD TO INHIBIT THE RETROVIRAL REPLICATION AND USE OF SUCH COMPOUNDS IN THE LABOR COMPOSITIONS AR035819A1 (en)

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US28770401P 2001-05-02 2001-05-02

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